1,2-Dichloroethane → (1R,2S)-Tranylcypromine

HRID 1619185Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[BH-](O[C:15]([CH3:17])=O)(OC(C)=O)OC(C)=O.[Na+].CCO[C:22]([CH3:24])=O.Cl[CH2:26][CH2:27]Cl>>[CH2:3]1[C@@H:1]([NH2:4])[C@@H:2]1[C:17]1[CH:15]=[CH:24][CH:22]=[CH:27][CH:26]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 8857Ethyl Acetate

HCID 69828Cyclopropylamine

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 19493(1R,2S)-Tranylcypromine

Conditions

Temperature: 25 °C

Procedure

A solution of trans-4-(cyclopropylamino)-1-(2-fluorophenyl)cyclohexanecarbonitrile (4.4 g, 20.2 mmol, 1.0 equiv.) in 1,2-dichloroethane (40 mL) was treated at 0° C. with cyclopropylamine (2.31 g, 40.4 mmol, 2.0 equiv.) and NaBH(OAc)3 (8.56 g, 40.4 mmol, 2.0 equiv.) successively. After being stirred at 25° C. for 12 h, the reaction mixture was diluted (EtOAc), washed (1×1 N NaOH and 2× brine), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 20% EtOAc/n-Hexane containing 2.5% of TEA) gave the trans amine as a colorless oil.

Workup

washwashed (1×1 N NaOH and 2× brine)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customPurification by flash chromatography (SiO2, 20% EtOAc/n-Hexane containing 2.5% of TEA)

Sources & evidence

ORD record: ord-9d2dd5472fb544ee8e3f1417a6b9adb3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772296B2

Reaction notes

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